Water → Topiramate

HRID 1380664Notes

Reaction equation

HRID 1380664 reaction equation
[H-].[Na+].S(Cl)(=O)(=O)N.O.[S:9](=[O:13])(=[O:12])([OH:11])[NH2:10].O[CH2:15][C@:16]1([O:25][CH2:24][C@@H:22]([OH:23])[C@@H:20]([OH:21])[C@@H:18]1[OH:19])[OH:17]>CN(C=O)C>[CH3:15][C:16]1([CH3:18])[O:21][C@@H:20]2[C@@H:22]([CH2:24][O:25][C@@:16]3([CH2:15][O:12][S:9]([NH2:10])(=[O:11])=[O:13])[O:17][C:22]([CH3:24])([CH3:20])[O:19][C@H:18]32)[O:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 131714623HCID 131714623, compound

Product 1

HCID 5284627Topiramate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold solution (-4° C.) of 2,3:4,5-di-O-isopropylidene-β-fructopyranose (75 g, 0.29 mol) in DMF (725 ml) was added 50% oily sodium hydride (16.34 g, 0.34 mol as NaH). After stirring for 90 min, sulfamoyl chloride (54.9 g, 0.48 mol) was added and the stirring continued for an additional 3.5 hr at that temperature. The reaction mixture was poured into cold water and extracted with toluene. The organic layer was dried (Na2SO4) and the solvents removed under vacuum to give a syrup which crystallized immediately. Recrystallization from ethylacetate/hexane gave pure 2,3:4,5-bis-O-methylethylidene)-β-D-fructopyranose sulfamate, mp 125°-126° C.

Workup

  1. waitthe stirring continued for an additional 3.5 hr at that temperature
  2. extractionextracted with toluene
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvents removed under vacuum
  5. customto give a syrup which
  6. customcrystallized immediately
  7. customRecrystallization from ethylacetate/hexane
  8. customgave pure 2,3

Sources & evidence

ORD record
ord-8404ca2c560a48afbe9e94cf58cab845
Source dataset
uspto-grants-1986_04
Patent number
US04582916

Reaction notes

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